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From 1,2-difunctionalisation to cyanide-transfer cascades – Pd-catalysed cyanosulfenylation of internal (oligo)alkynes

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Abstract

Internal alkynes substituted by aliphatic or aromatic moieties or by heteroatoms were converted into sulphur-substituted acrylonitrile derivatives. Key is the use of Pd catalysis, which allows the addition of aromatic and aliphatic thiocyanates in an intra- and intermolecular manner. Substrates with several alkyne units underwent further carbopalladation steps after the initial thiopalladation step, thus generating in a cascade-like fashion an oligoene unit with sulphur at one terminus and the cyano group at the other.

Graphical abstract: From 1,2-difunctionalisation to cyanide-transfer cascades – Pd-catalysed cyanosulfenylation of internal (oligo)alkynes

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Article information


Submitted
10 Sep 2019
Accepted
22 Dec 2019
First published
23 Dec 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

From 1,2-difunctionalisation to cyanide-transfer cascades – Pd-catalysed cyanosulfenylation of internal (oligo)alkynes

M. Bürger, M. N. Loch, P. G. Jones and D. B. Werz, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC04569D

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